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Molecules 2013, 18(12), 14961-14976; doi:10.3390/molecules181214961

Synthesis, Spectroscopic and Semiempirical Studies of New Quaternary Alkylammonium Conjugates of Sterols

Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland
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Received: 6 November 2013 / Revised: 27 November 2013 / Accepted: 28 November 2013 / Published: 5 December 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

New quaternary alkylammonium conjugates of steroids were obtained by two step reaction of sterols (ergosterol, cholesterol, dihydrocholesterol) with bromoacetic acid bromide, followed by bimolecular nucleophilic substitution with a long chain tertiary alkylamine. The structures of products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. The pharmacotherapeutic potential of synthesized compounds has been estimated on the basis of Prediction of Activity Spectra for Substances (PASS).
Keywords: sterols; quaternary alkylammonium salt; conjugates; Prediction of Activity Spectra for Substances; PM5 calculations sterols; quaternary alkylammonium salt; conjugates; Prediction of Activity Spectra for Substances; PM5 calculations
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Brycki, B.; Koenig, H.; Kowalczyk, I.; Pospieszny, T. Synthesis, Spectroscopic and Semiempirical Studies of New Quaternary Alkylammonium Conjugates of Sterols. Molecules 2013, 18, 14961-14976.

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